Obtaining Demoman achievements

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Air Raid
Air Raid
Kill 3 players during the same parachute deploy.
Difficulty: Medium-Hard
How to obtain: You need the B.A.S.E. Jumper as your primary weapon and a Stickybomb Launcher as your secondary weapon. Sticky jump high above a group of enemies, deploy your parachute, and try to obtain three kills before you land.


Beat Me Up, Scotty
Beat Me Up, Scotty
Use a critical swing with the Eyelander to kill 5 enemy players.
Difficulty: Easy-Medium
How to obtain: Any of the Demoman's shields will grant critical melee hits on a full charge. Alternate methods of obtaining guaranteed mini-crits and full crits include friendly Jarate, the Kritzkrieg ÜberCharge, securing the enemy Intelligence, or acquiring First Blood in Arena.


Blind Fire
Blind Fire
Destroy an Engineer building that you can't see with a direct hit from your Grenade Launcher.
Difficulty: Medium
How to obtain: Hide behind cover to safely lob grenades at enemy buildings. Aim carefully, as you cannot bounce grenades off walls to accomplish this. Alternatively, you can fire grenades at a building in plain sight, then take cover before they hit.


Bloody Merry
Bloody Merry
Provide an enemy player with a freeze cam of your smiling face.
Difficulty: Very Easy
How to obtain: Taunt with your Grenade Launcher, Loch-n-Load, Pain Train, or Loose Cannon equipped immediately upon killing an enemy.


Brainspotting
Brainspotting
Decapitate 50 enemy players.
Difficulty: Medium
How to obtain: Equip one of the Demoman's bladed melee weapons to decapitate enemies. The charge ability offered by any of the Demoman's shields allows you to quickly reach enemies that are outside melee range. Certain weapon bonuses, like the Eyelander's head gathering mechanic or Tide Turner's recharge-on-kill, can help get consecutive melee kills.


Bravehurt
Bravehurt
Kill 25 players defending a capture point or cart.
Difficulty: Easy-Medium
How to obtain: When your team is capturing a point, fire grenades at nearby defenders and lay Stickybombs to prevent reinforcements from interfering.


Caber Toss
Caber Toss
Bounce an enemy into the air and kill them before they land.
Difficulty: Medium
How to obtain: Any of the Demoman's explosive weapons can be used to send an enemy into the air. Before your foe hits the ground, finish him off with a well-placed grenade or Stickybomb.


Chain Reaction
Chain Reaction
Get 3 kills within 6 seconds using the Demoman charge.
Difficulty: Medium-Hard
How to obtain: You will need to use the shield charge three times in quick succession, grabbing a kill each time. The Tide Turner is required for this achievement, as it is the only shield that can allow you to charge multiple times over six seconds. Plan ahead; look for more enemies even before each kill to ensure your killstreak doesn't break.


Cry Some Moor!
Cry Some Moor!
Destroy 50 buildings.
Difficulty: Easy
How to obtain: The Demoman excels at building destruction. Coordinate with friendly Medics to take out problematic Sentry Guns. It is recommended to equip either the Stickybomb Launcher or Scottish Resistance, as detonating multiple Stickybombs at once can instantly destroy any building.


Double Mauled Scotch
Double Mauled Scotch
Kill 2 people in a single sticky jump.
Difficulty: Medium-Hard
How to obtain: Sticky jump above a group of enemies and rapidly fire your projectiles at them. Any enemies killed by Stickybombs detonated in the same explosion as your jump will count towards this achievement.


Flight Control
Flight Control
Kill a parachuting player while parachuting.
Difficulty: Medium
How to obtain: The B.A.S.E. Jumper is required for this achievement. If an enemy Soldier or Demoman deploys his parachute, he becomes an easy target. Sticky jump upwards and target him with air-detonated Stickybombs or your melee weapon.


Glasg0wned
Glasg0wned
Kill 25 Scouts and Pyros with the Grenade Launcher.
Difficulty: Medium
How to obtain: Both of these classes have the advantage over you at closer ranges. Pyros can use the compression blast to reflect your grenades back at you, while Scouts have enough speed to easily dodge your grenades. Use prediction and good aim to pick them off at a distance.


He Who Celt It
He Who Celt It
Use the Sticky Launcher to kill an enemy player via environmental damage.
Difficulty: Medium
How to obtain: When blasting an enemy into the air with a Stickybomb, try to make sure that they will either die from the resulting fall damage or fly into an environmental hazard such as a bottomless pit.


Head-On Collision
Head-On Collision
Kill a charging Demoman while charging.
Difficulty: Medium
How to obtain: Match an enemy Demoman's shield charge with your own. Once you reach each other, be the one to swing your melee weapon first.


Highland Fling
Highland Fling
Sticky jump a really long way...
Difficulty: Easy-Medium
How to obtain: The achievement is based on the horizontal distance covered by your Sticky jump. In standard play, you will need to use two or three Stickybombs to cover the required distance. The estimated length you need to travel can be measured by the distance from the first BLU spawn on Badwater Basin to the first capture point. While attempting this will generally leave you near death, if not dead, the Sticky Jumper can be used to nullify self-damage while obtaining this achievement.


Kilt in Action
Kilt in Action
Kill 500 enemy Soldiers.
Difficulty: Medium
How to obtain: Use class advantages to engage Soldiers on your own terms. Deny them a direct line of sight, lay sticky traps to halt their progress, and bounce grenades around corners. Continue to fight indirectly, as the Shotgun and Equalizer outdamage your melee weapons.


Laddy Macdeth
Laddy Macdeth
Kill 50 enemies with direct hits from the Grenade Launcher.
Difficulty: Medium
How to obtain: Take into account the arced trajectory of your grenades to land direct hits on your enemies.


Left 4 Heads
Left 4 Heads
Decapitate 4 players with only 10 seconds between each kill.
Difficulty: Hard
How to obtain: For this achievement, use any bladed melee weapon such as the Eyelander, which decapitates enemies on kill. Pair your melee weapon with any Demoman shield and use the charge ability to reach new targets before the ten seconds expire. Enemies tend to be more clustered and often within melee range in Medieval Mode.


Loch Ness Bombster
Loch Ness Bombster
Kill an enemy player with sticky bombs within 5 seconds of them teleporting.
Difficulty: Medium
How to obtain: Lay Stickybombs at an enemy Teleporter Exit. Wait for someone to use the Teleporter, then detonate your trap. An enemy with the telltale glow underneath their feet is a sure sign that a Teleporter is nearby.


Operation High Dive
Operation High Dive
Parachute 19.47 miles.
Difficulty: Easy
How to obtain: This achievment will be obtained naturally after a good amount of time, as long as you regularly deploy the B.A.S.E. Jumper to parachute long distances.


Pipebagger
Pipebagger
Kill at least three players with a single detonation of sticky bombs.
Difficulty: Easy-Medium
How to obtain: Conceal Stickybombs in multiple contested areas where players tend to gather. Detonate your traps after enough enemies have arrived. Alternatively, have a Medic assist you with the Kritzkrieg; just one critical Stickybomb can gib many players at once.


Robbed Royal
Robbed Royal
Destroy 100 enemy sticky bombs with the Scottish Resistance.
Difficulty: Easy
How to obtain: Try to predict where enemy Demomen would place Sticky traps. If their Stickybombs are clustered together, you can use just one or two to destroy them all.


Scotch Guard
Scotch Guard
Kill 3 enemies capping or pushing a cart in a single Stickybomb detonation 3 separate times.
Difficulty: Medium
How to obtain: Hide Stickybombs around Control Points or at locations the Payload cart must pass through and detonate your trap once enough enemies have gathered.


Scotch Tap
Scotch Tap
Glory in the slaughter of your enemies using the Eyelander.
Difficulty: Medium-Hard
How to obtain: Find an unaware enemy, such as a scoped Sniper, and perform the Eyelander, Horseless Headless Horsemann's Headtaker, Claidheamh Mòr, Half-Zatoichi, Persian Persuader, or Nessie's Nine Iron's taunt on them. While the taunt does take a considerable amount of time, it is also one of the quietest, allowing you to attempt it multiple times on the same target.


Second Eye
Second Eye
Provide an enemy player with a freeze cam of you shaking your rump.
Difficulty: Very Easy
How to obtain: Upon killing an enemy, taunt with the Scottish Resistance equipped.


Shorn Connery
Shorn Connery
Decapitate a cloaked Spy.
Difficulty: Medium
How to obtain: You will need a bladed melee weapon that can decapitate enemies, such as the Eyelander. You may incidentally see a cloaked Spy that bumps into either you or your teammates. When this happens, unsheath your blade and chase him down. If you know a Spy is nearby, randomly swinging your weapon a few times won't hurt either.


Slammy Slayvis Woundya
Slammy Slayvis Woundya
Decapitate an enemy Soldier who is brandishing the Equalizer.
Difficulty: Medium
How to obtain: A Soldier with the Equalizer out will often already be wounded, causing him to outdamage you. Most of your bladed melee weapons have an increased melee range, so space yourself well to avoid being hit.


Something Stickied This Way Comes
Something Stickied This Way Comes
Kill 30 players with air burst sticky bombs.
Difficulty: Medium
How to obtain: Stickybombs cannot be detonated for roughly a second after being fired. Aim above enemies and detonate your Stickybombs before they touch the ground. Charged, long range Stickybombs can be used to “snipe” targets that are far away.


Spynal Tap
Spynal Tap
Kill 20 spies within 5 seconds of them sapping a friendly building.
Difficulty: Easy-Medium
How to obtain: Guard friendly buildings by placing Stickybombs nearby, detonating them once you see or hear a Spy. If you have no sticky traps laid, chase after the Spy with your Grenade Launcher or melee weapon.


Sticky Thump
Sticky Thump
Using the Scottish Resistance, kill 3 players in separate explosions without placing new sticky bombs.
Difficulty: Medium
How to obtain: Lay sticky traps at multiple chokepoints while watching for any enemies to pass. If you fire another Stickybomb after a kill has been obtained, your progress will be reset.


Tam O'Shatter
Tam O'Shatter
Destroy 5 enemy Engineer buildings during a single ÜberCharge from a Medic.
Difficulty: Hard
How to obtain: This achievement coincides with “Medical Breakthrough”, a corresponding achievement for the Medic. While the Demoman excels at destroying buildings, the difficult part of this achievement is finding five buildings to destroy in the eight seconds an ÜberCharge is active. Be very aggressive and lay multiple Stickybombs around these buildings. It will take three Stickybombs at most to destroy any building that is not shielded by the Wrangler. Rather than waste time reloading the Stickybomb Launcher, switch to your Grenade Launcher to finish off any remaining buildings.


Tartan Spartan
Tartan Spartan
Do 1 million points of total blast damage.
Difficulty: Easy
How to obtain: The Demoman can deal explosive blast damage using his Grenade Launcher, Loch-n-Load, Stickybomb Launcher, Scottish Resistance, and Ullapool Caber. You will naturally obtain this achievement after quite some time playing as the Demoman.


The Argyle Sap
The Argyle Sap
Blow up an Engineer, his sentry gun, and his dispenser with a single Sticky bomb detonation.
Difficulty: Easy
How to obtain: When you encounter an Engineer's nest of buildings, lay a carpet of Stickybombs around the required buildings and the Engineer himself before detonating any of them. It will take a maximum of six Stickybombs to destroy a Sentry Gun shielded by the Wrangler. If the nest is in an area that is hard to reach, have a Medic assist you with an ÜberCharge.


The High Road
The High Road
Sticky jump onto a cap point and capture it.
Difficulty: Easy-Medium
How to obtain: It will be easier to attempt this on a standard Control Point map, where capture times are significantly shorter. Because you must be on the point for the entire duration of the capture, equipping the Pain Train and having teammates assist you are strongly recommended.


There Can Be Only One
There Can Be Only One
Decapitate your nemesis.
Difficulty: Medium
How to obtain: Sticky jump or charge with any shield to quickly close the gap between you and your nemesis. Use the Eyelander, Scotsman's Skullcutter, Horseless Headless Horsemann's Headtaker, Claidheamh Mòr, Half-Zatoichi, Persian Persuader, or Nessie's Nine Iron to get the kill.


The Scottish Play
The Scottish Play
Get a melee kill while sticky jumping.
Difficulty: Hard
How to obtain: Air strafe as you Sticky jump in order to reach a moving target. This feat can be performed as you collide with another midair player or as you land on an enemy's head.


The Targe Charge
The Targe Charge
Charge and kill someone with your shield bash.
Difficulty: Medium
How to obtain: For this achievement, it may be easiest to use the Splendid Screen, which unlike the Chargin' Targe, can deal damage during any point of your charge. The shield bash deals only a moderate amount of damage, so chase down weakened players and resist the urge to swing your melee weapon.


The Stickening
The Stickening
Kill 3 Heavies from full health with a single sticky bomb detonation.
Difficulty: Medium
How to obtain: A Heavy in a contested area is not likely to be at full health, so catch him by surprise elsewhere with a carefully concealed sticky trap. If you see an ÜberCharged Heavy, lay at least five Stickybombs at his feet and detonate them once the charge wears off.


Three Times a Laddy
Three Times a Laddy
Dominate three Engineers.
Difficulty: Easy
How to obtain: A Demoman can often wipe out an Engineer and any of his nearby buildings with a single detonation of Stickybombs. Use your indirect weaponry to safely take out Engineer nests from behind cover. Beware that the Engineer's weapons are moderately powerful at close-range; Revenge crits from the Frontier Justice can end your Domination attempts very quickly.


U-Turn
U-Turn
Kill an enemy that you couldn't see at the beginning of your charge.
Difficulty: Medium
How to obtain: There are two likely ways to obtain this achievement. First, you can wait in a narrow corridor that limits your vision and predict when an enemy will appear before charging. Alternatively, you can use the Tide Turner's full turning control to fulfill these conditions out in the open.


Well Plaid!
Well Plaid!
Kill 10 enemies while assisting or being assisted by another Demoman.
Difficulty: Easy
How to obtain: Coordinate with friendly Demomen to destroy the same targets, taking advantage of the large splash damage offered by your explosive weaponry.